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He was trained as a lawyer before entering theological college, and was ordained to the ministry in 1969. While studying theology in Chicago (McCormick Theological Seminary) he worked for noted social activist Saul Alinsky. In his career, Phipps has worked as a poverty lawyer, community organizer and pastor. From 1974 to 1983, he was minister at Trinity-St. Paul's United Church in downtown Toronto, Ontario. After leaving Trinity-St. Paul's United, he moved to Alberta to work in church administration.

A theological liberal, Phipps engendered controversy when shortly after becoming moderator he said "I don't believe Jesus was God", that he didn't consider the resurrection a scientific fact, and that he was agnostic on the question of an afterlife. What is important, Phipps argued, is not notions of the afterlife but fighting poverty and suffering on earth. "Your soul is lost unless you care about people starving in the streets," according to Phipps. He said that what is important is not so much whether or not the Bible is a literal historical record but the teachings and example of Jesus. This sparked great debate in the church, with some congregations passing motions asserting their faith in Jesus' literal resurrection.

Phipps was in the news again on April 1, 2005, when he was quoted in the Calgary Herald sharply attacking the Roman CatholicBishop of Calgary, Frederick Henry. The occasion was the laying of two human rights complaints against the bishop for reaffirming the traditional Catholic teaching on homosexuality in a letter to the Catholics of his diocese. There was some objection to the strength of Henry's statements.

Phipps was quoted as saying the following:

"He portrays himself as a victim. Well, please."

"Why are we focusing on one bishop who loves the spotlight?"

"This is about a group who have been maligned, who have been beaten up physically, mentally and spiritually."

Phipps' views contrasted with those of the Alberta Civil Liberties Association, and conservative Jewish, Muslim, Sikh and Mormon leaders who saw the issue as one of religious freedom.